Chicago: For Your First Weekend Visit

I often get asked by folks about to visit Chicago, or have friends about to visit Chicago, “What are the best things to do in Chicago?” I didn’t grow up here, but moved here about 7 years ago. Since then, I have been somewhat a student of the city, and I love to share my discoveries. Here is a little list about what I would suggest if you are heading in for a weekend and have never been here before.

Where to stay:

  • The W City Center: Just one of my favorite hotels. There are MANY, but I will just include this one for now, as it is very well placed for what I am going to suggest to do with your time.

Where to walk to from there:

  • Make sure to peak into the lobby of Daniel Burnham’s beautiful updated hotel
  • then go across the street to admire Picasso’s amazing gift to the city.
  • From there, head to Marshall Field’s turned Macy’s. My incredible friend Shannon once dubbed this “The Mother Ship”, and I think that is a perfect description. Make sure to examine the exterior architecture and interior Tiffany dome.
  • If you are feeling brave – you may wish go check out the Willis Tower (formally the Sears Tower) which has a new all glass observation deck (even the floor is glass) so the views from one of the tallest buildings in the world become almost 360º. I have not been up there yet, but am really excited to do so soon.
  • Make sure you take a stroll down the Magnificent Mile. This starts at Michigan Ave. just north of the bridge after Wacker Dr. and goes for – you guessed it – a mile. Along this stretch there are at least 4 or 5 full sized malls, and countless storefronts. Don’t forget to examine the outer walls of the Tribune Tower, which are adorned with pieces of great architectural sites from around the world (ie Taj Mahal, the Parthenon, the Great Pyramid, The Alamo, and Notre-Dame to name a few).
  • Check out Millennium Park – and be amazed at what an ambitious mayor can make happen! Be sure to check out the great art sculptures, like Cloud Gate – or what the locals refer to as ‘The Bean’. Part of its charm, I think, is its popularity. You won’t be able to help but snap a panoramic city photograph of yourself in its reflection.
  • Take a ride on the El! The El is the elevated train, and one of the greatest and cheapest ways to see the city. Get on the Brown line and take it around the loop to enjoy this quintessential view of Chicago.
  • Weather permitting, don’t miss an Architectural Boat tour along the river, showcasing the city’s great building. Follow the link for my favorite choice.
  • Have a cocktail to finish off your day on the 95th floor of the Hancock Tower.

Don’t miss out on these Chicago things to eat:

  • Deep Dish Pizza
  • Chicago Style Hot Dog
  • Italian Beef
  • Garrett’s Popcorn
  • The amazing restaurant options in this town are astounding. For this, I will refer you to what I think is the best dining guide in the city.

There are many things I left out, but perhaps I will do a follow up trip posting another day. Have a GREAT time in The Windy City, The City of Broad Shoulders, The City by the Lake, The City That Works, My Kind of Town… Chicago.

View from the 95th floor of The Hancock Tower

View from the 95th floor of The Hancock Tower looking south down Michigan Ave.

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